The Sinner
by Vampire Weekend
Summary: Castiel’s first time. Dean/Castiel. Contains smut, shmoopiness and slash. Challenge by shion kun. One-shot.


Summary: Castiel's first time. Dean/Castiel. Contains smut, shmoopiness and slash. Challenge by shion_kun. One-shot.

Rating: M for mature.

Warnings: Smut and slash.

Pairing: Dean/Castiel

I don't own Supernatural. I've never owned Supernatural. There is an excellent chance that I will never own Supernatural. Please don't sue. I don't have enough money to get a good lawyer. I also don't own the quote at the beginning of the chapter. I think it's brilliant, though.

Not only is this my first story with Castiel and Dean as a couple, instead of my usual Sam and Dean, this is also my first ever smut story. So, as you can imagine, I was extremely hesitant to even post this. Hopefully, I did the characters justice and I didn't mess up too badly.

Also, major kudos to **shion_kun** for giving me the idea.

**The Sinner**

_-_

_The angels are so enamored of the language that is spoken in heaven that they will not distort their lips with the hissing and unmusical dialects of men, but speak their own, whether their be any who understand it or not. _

_Ralph Waldo__ Emerson_

-

It was not like Dean to sleep with a bumbling, nervous virgin. Well, when he was younger, sure, but that was just because he had such limited options then. No self-respecting twenty-five year old woman would want to sleep with a sixteen-year old. But now, no, he liked experienced women. Women who knew what they were doing, women who wouldn't hesitate to tell him what they wanted.

So, it was an odd predicament that, at that moment, Dean was face-to-face with a blushing, almost painfully virginal, Castiel.

"You okay there?" Dean asked, rubbing the back of his neck, a gesture that clearly showed how uncomfortable he was.

"I am fine," Castiel assured him. "Are you okay?"

Dean swallowed but nodded his head quickly. "I want this and you want this too, right? I mean, so why shouldn't we be doing this?"

The angel shrugged, taking off his jacket and pulling off his shirt, exposing his stomach. On it were two large scars, each of them white and pale, like they had been there for a long time. "How did you get these?" Dean gestured towards his stomach. "The scars, I mean."

"This is not my body, Dean. I have no idea how he got them."

"Right, right," he stepped closer to Castiel, taking a deep breath before inquiring, "can I kiss you?"

A pause.

"Yes."

To say that the kiss was like inhaling a breath of fresh air was an understatement. Sure, it was awkward and a little clumsy; a fault of both parties, but it was a feeling that Dean had never felt. He was afraid that Castiel could hear his rapid heart pounding in his body.

Dean started to peel the clothes off of himself, breaking the kiss momentarily so he could take off his shirt.

He looked at the motel bed through the corner of his bed. It was barely big enough for the both of them but, though it wasn't too comfortable, it would have to suffice. Apparently, there was a Star Trek convention the next town over and all the Trekkies were filling up the motels. Damn Trekkies.

"Are," Dean was embarrassed at how out of breath he sounded. "Are you sure about this?"

"I am," as always, Castiel's face was unreadable but the damp tent in the angel's pants was enough to tell Dean what the angel was really feeling.

"Take off your pants," the man instructed, helping Castiel unzip.

"It hurts."

Alarmed, the human stopped what he was doing and looked up. "What does?"

Glory, Dean never knew that Castiel could blush, but there it was, making his face look healthy rather then embarrassed. "Down. It hurts."

"I'm unzipping your pants right now. It'll still hurt but it won't hurt as much."

Castiel couldn't help but moan when his hard member was finally released out into the open, the cold air hitting it.

"Does it feel better?"

Castiel captured Dean's mouth in a long kiss before muttering, "Much."

Dean slowly moved the angel to the bed, pushing him on it and then straddling him, kissing his chest.

"This okay?"

"Yes."

Dean did what he liked when girls did it to him. He licked Castiel's hard nipple, making sure it was nice and wet, before blowing on it.

Castiel made a strangled noise and that only seemed to encourage Dean. He could feel the angel's hard member pressing against his legs and lightly touched it, trying to get a feel of what he was actually doing. Once he got past the, 'Oh my god, I'm touching another guy's penis!' it was actually kind of nice. The noises Castiel was making was pure heaven, pun fully intended, and Dean decided to go for it.

"So you want to go all the way?"

"What would all the way include?"

"Having sex."

Another pause.

"How would we do that?"

This time, it was Dean who was blushing.

"Um, I could, you know, put my penis in your ass or you could do that to me if you want. I don't mind either way."

"It sounds painful."

"I've never done this before," Dean stated. "With another guy before but I think the pain goes away."

"You can be the one to put it in me, Dean."

"Okay. Uh, lie on your back."

Castiel did so and, still with an achingly hard erection, Dean got up, opened his duffel bag and pulled out the small bottle of KY.

"Put your legs on my shoulders."

Castiel did so and Dean struggled not lean one way because of the added weight.

"Talk me through this," Castiel said, looking at Dean with his trusting blue eyes.

Dean nodded, coating his fingers with the lubricant. "I'm going to put this in you. Tell me if it hurts too much and I'll stop."

The human waited for a response but realized that he was not going to receive one and he slowly found Castiel's vessel's hole and carefully pushed one finger inside it. The angel hissed.

"Does it hurt?"

"Burns," Castiel looked expectantly at Dean. "Keep going. It's going to start feeling good soon, right?"

"It's supposed to."

Dean moved his finger around a little until he hit a small bump and a loud groan escaped from the angel's lips.

"Are you okay?"

"What was that?

"I think that's your prostate. It's supposed to feel good."

"It does."

"I'm going to add another finger."

Dean had to whine a little too. With just two fingers, it was already so tight. He wondered what it would feel like to put his member in it, if it too would be strangled.

"One more finger should do it."

By now, Castiel had lost all of his composure and was pushing wantonly against the fingers inside of him.

"Please, please," the angel pleaded.

Dean nodded, drizzling some lubricant over his erection. "You ready for this?"

"Please, please," Castiel repeated.

"Okay."

And with a painfully slow push, Dean entered Castiel.

Castiel winced in pain when, reflexively, Dean bucked up his hips. "Wait, Dean. Hold on," he took a moment and then breathed. "Go."

The heat surrounding him was the most amazing thing Dean had ever felt. Screw that slut that was trying to pick him up at the bar last night. Screw everything and everyone. He had Castiel now. He was _in_ Castiel now.

Castiel, being his first time, came quickly and when he did, a feeling of pure nirvana washed over him.

With a few more thrusts of his hips, Dean came inside Castiel. With a few tugs, he took his now limp member out and spooned Castiel.

"You alright?"

Castiel turned his head to look at the human he had grown so fond of. "Yes."

_Fin_

Thanks for reading. I hope the smut scene wasn't too painful to read. Any and all reviews are appreciated.

As always, I will respond to any review I receive as long as I can find the email address.


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